Madonna Singles Ranked, 91-101

(Every few days or weeks, I pick a music artist or band, compile a chronological playlist of all of their singles (based on Wikipedia, Discogs and a few other sources) and then try to arrange that playlist in such a way that I like each song more than the previous song. Rearranging the songs is a never ending process so once I’m at a point where I think I’m pretty close to how I feel, I share the results with you 10 or so songs at a time. I’ve come to define “singles” in a pretty broad way so that it includes any song that was used to promote an album (via video or single) or any song that charted in a significant way. Generally speaking, I don’t include remixes or live versions of songs that were previously released as singles.)

Between 1983 (when her first album was released) and 2015 (when her most recent album came out), Madonna has had one of the most continuously successful careers in music. Setting aside the occasional blip in sales, her albums have always reached the top of the charts and she typically has a couple of top 10 hits from each album (typically on the pop charts but at the very least on the dance charts). You can read some of her many achievements at Wikipedia so I won’t repeat them here.

I can’t talk about Madonna without addressing my teenage misogyny. When Madonna first came to my attention, her early songs (like “Lucky Star,” “Into The Groove” and “Borderline”) were getting airplay on our local college station, WXCI. Her dance/synth grooves fit in perfectly next to 1983 era Depeche Mode and Yaz. When those songs first started to chart, there was a brief moment where I felt like “hurray, one of our artists is breaking in!” Then, however, girls really started liking Madonna.

Now, any woman or girl who has been around boys or men who are obsessive about a subject have surely experienced ad nauseum the behavior I exhibited. I didn’t recognize it at the time, but just the fact that lots of girls liked an artist signaled to my teenage brain that there was something wrong with that artist and I should vocally reject them. At the time, I had other reasons for disliking her (which I’ve pretty much forgotten now, but probably boiled down to “sell out,” which is ridiculous) but if I’m being totally honest with myself all these years later, if I liked something that a bunch of other people (particularly girls) liked, then I couldn’t hold my taste up as being superior to everyone else’s.

The irony here is that the two people who were the taste-setters for me in terms of music in that era were women (Hi Christie! Hi Lynne!). I was perfectly happy rejecting things every other woman liked just because I “obviously” knew more than them. Anyhow, I’m not proud of this and I’m glad I grew out of it (at least to the extent that I know I do it and fight my own impulses like crazy whenever I feel the word “actually” forming in my mouth).

So, as I start writing about Madonna, I have some very specific prejudices that have been vexing me. First, I have a visceral reaction to all of her songs up to the Like a Prayer album (which wasn’t the record that won me over but which, in retrospect, was the first one I really liked) and this reaction makes it hard for me to gauge the songs fairly. Second, I find that I tend to scrutinize her songs from all eras much more closely than I do with other artists (even other female artists) because I feel a need to justify (to my 15 year old self) why I like them. This means I have been overthinking her songs like crazy and my rankings, as a result, have been extremely volatile – a song I placed in the top 20 could drop to the bottom 20 and vice versa. Finally, I fight an impulse to hold her to a higher standard than I hold other artists. For example, R.E.M.’s sound is largely effected by their choice of producers (Mitch Easter was an essential part of the jangle rock sound on their first records). I almost never think about the various non-R.E.M. entities that helped shape their sound and success. With Madonna, I spent a lot of time pondering her producers and their impact on her success – as if her conscious artistic choices regarding collaborators was a bigger deal than R.E.M.’s.

I’ve tried to come up with a basic set of assumptions about how I interact with music so that I can hold Madonna to the same (low) standard to which I hold other artists. First, I assume that everything a musician does on a song is a deliberate choice and credit those choices to the musician. Second, I recognize that my personal feelings about songs (which is what these lists are about) are a separate thing from the relative impact or importance of a song. Third, if I don’t have a rational reason for disliking a song, that’s ok, but I need to acknowledge the irrationality instead of inventing a reason why I don’t like it. Finally, I remind myself that I’m looking at these songs as singles and not in context of the album or movies that they’re from. I can’t always do that (Evita) but I try.

OK, let’s do this. I think I have at least two or three choices that are maddening per section of this list.

101. Shine a Light

1992 Bootleg Single of a 1979/80 Unreleased Song

This might be the least controversial choice on this list. Madonna didn’t choose to release this song – it was released as a bootleg single in 1992. It allegedly got a bunch of airplay in Europe so I felt I had to include it. Madonna sings and plays guitar on this song. At the time, she was clearly going for the rock and roll thing. Its not so much that the song is bad – its just poorly produced (because it was a demo and not really meant for the public) and sort of unremarkable. Unreleased recordings have a certain academic value but releasing this song was an illegal cash grab that went against the artist’s wishes, so basically down with this track!

100. Act of Contrition

From 1989’s Like A Prayer, Acetate Single

Acetate singles are a kind of single that can be played about ten times before wearing out. They are made individually so they’re very rare – typically, they’re made to share with a radio station so it can play the song a few times but they’re not intended for mass play. “Act of Contrition” is a brilliant ending to the Like a Prayer album. The lyrics are mostly Madonna praying (which obviously fits in perfectly with the themes of the record), there’s some blistering guitar work from Prince and the punchline of the song is funny at least the first time you hear it. Apart from the album, its a little bit mystifying. Its too short to be a dance song and not really catchy enough to be a pop hit. I’m sure there was a reason that this song was pressed (even in a limited form) but I really have to fight the urge to skip over it almost every time it comes on my iPod. Like sometimes I have to use my left hand to restrain my right hand from pressing skip. On the other hand, when I listen to the whole album, this is a welcome little coda. Context, people.

99. Gambler

From the soundtrack of the 1985 film Vision Quest, Second Single

Listening to 80’s era Madonna was a real challenge for me. As I said above, I have a visceral reaction to most of her songs from this period (“TURN IT OFF”) that is irrational and has nothing to do with the actual relative quality of the song. Sometimes, it even has nothing to do with whether I even like a song or not (for example, “Get Into The Groove” is a fantastic song and my lizard brain even wants me to reject that one). That all said, I really don’t like this song. Part of this is because it screams “80’s production values.” Part of it is that I dislike that little rattly drum sound that was so popular in that era. Part of it is just the song itself is trite and dull – Madonna was creating some great pop in the mid-80’s and this sounds more like a throw away tune than something deserving of individual attention. This is the first song on this list that I dislike for itself rather than for its context.

98. Another Suitcase in Another Hall

From the soundtrack to the 1996 film version of Evita, Fourth Single

No no no no. OK, look. The whole point of this song in the original stage version of the musical is that Eva has walked over another woman to secure a new role as the mistress (and eventually wife) of Juan Peron. The song is sung by the mistress as she’s just been kicked out of Peron’s apartment by Eva. Che’s counter-vocal is slightly brilliant – he keeps saying “she’ll get by she always has before,” but in the end he tacitly acknowledges that he’s going to look away from her potentially dire fate (“don’t ask anymore”). In the film, they gave this song to Eva (Madonna) and completely changed its meaning. Its basically Eva giving herself a pep talk after walking out on a pre-Juan Peron lover. The voice telling her “she’ll get by” at the end is sort of her own interior monologue. Che’s “don’t ask anymore” line is at best diminished and at worst a non-sequiter. Ugh. I am trying so hard to look at these singles as singles and not in context of their sources, but I can’t ignore this. I get pissed off every time I listen to this. In this case, I’m going to hold director Alan Parker responsible, acknowledge that Madonna does a decent enough job singing it and just wretch.

97. Over and Over

From 1984’s Like A Virgin, released as a single in the Philippines only

Hey kids, want to know what every high school dance sounded like for 4 hours every single time in the USA in the 1980’s? If you were lucky, the Dj would slip in “Tainted Love” or “Dancing with Myself” or maybe Otis Day and The Nights’ “Shout.” For most of the night, it would sound like this song though. Not necessarily this song in specific, but a hundred songs that sounded just like this one. “Over and Over” was not released as a single in the U.S. so I’ve only had to endure it during this particular project. “Endure” is the operative word.

96. Superstar

From the 2012 album MDNA, released as a single in Brazil only

Hmm. OK, so I could almost give this song a pass on the “ooh la la” chorus and I’m sold on the production and beat. The lyrics, though. Uh, well, in general its about this guy that has the best qualities of Michael Jordan, Abe Lincoln, Al Capone (!!!), Caesar, Bruce Lee, John Travolta and James Dean. Let’s talk about that last one. She admires that he’s like James Dean driving fast in his car. Two thing. First, I just don’t get the admiration for somebody who drives fast. Second, driving fast really didn’t work out too well for James Dean. I’m assuming this was a deliberate choice on Madonna’s part and she’s maybe being funny or possibly she’s playing on the images of the characters she’s describing rather than the substance. I can’t get past it though – this dude she’s describing sounds kind of horrible.

95. Everybody

From 1983’s Madonna, First Single

This was Madonna’s first single from her first album (which had several much, much better songs). In essence, she wants everybody to get up and sing. Also, she wants everybody to do their thing. What their thing might be is not specified, so I’m assuming if field hockey or robotics or whatever is your thing, she wants you to do that. This is a dance tune and I really shouldn’t be mocking the lyrics – I mean, really, between the beat and her singing about getting up and dancing, the song takes its role pretty seriously. It even has a kind of neat swooping little keyboard thing going on. Still, as with most early Madonna, my brain just can’t take it. I think its one of her weaker songs and, since it was her first, I’m pleased to report that she made much, much better songs later – and even on the same album.

94. Where’s The Party

From 1986’s True Blue, released as a single in the Philippines only

OK, True Blue is my least favorite Madonna album. “Where’s the Party” is a song about being a person who loved to party in high school, couldn’t wait to grow up and then was surprised that being an adult meant that they have to work a job so they can cut loose on the weekend. No kidding, these are all classic pop music themes. Teenagers of all generations are distressed at how much work it takes to support an active social life when they become adults (and it doesn’t get any easier, kids). That said, Madonna was already starting to move away from this sort of sound by 1986 (listen to how different even “Papa Don’t Preach” from this same album sounded) and this tune sounds like she’s already over it. I don’t think its a coincidence that several of the songs I’ve ranked here at the bottom weren’t released as singles in the US.

93. Hanky Panky

From 1990’s I’m Breathless: Music From and Inspired By Film Dick Tracy, Second Single

Oh lord, Dick Tracy. I was working at Harwich Junior Theatre on Cape Cod in the summer of 1990 with my good friend Scott Dalton. When I would go to the convenience store, I’d by Hostess Orange Cupcakes, a Pepsi and a pack of Dick Tracy cards. At first, I was collecting them ironically, but I became seriously obsessed with collecting them all. The movie was a disappointment and suggested to me that Hollywood had taken the wrong lesson from the success of Tim Burton’s Batman. They thought we liked it because he was a comic hero – just like Dick Tracy! But we actually liked it because he was Batman. Anyhow, “Hanky Panky” is a song about how she enjoys dating mean dudes who are willing to treat her badly and, ultimately, spank her. Whatever you’re into, I guess. I think the song is intended to be… cheeky? I don’t know, the playfulness seems forced to me and I find the production on this song to be kind of disappointing – I think a more full sound would have made it work a little better. This was an issue with the film in general, though – they got so many things write but something about it just didn’t click.

92. Rain

From the 1992 album Erotica, Fifth Single

I don’t have a whole lot to say about “Rain.” After her Truth or Dare movie, I was pretty sold on Madonna as a serious artist. I was starting to come around to liking her music as early as Like a Prayer and I was sold on her by “Vogue,” so Erotica was the first album that I listened to as a record. I recall it not being especially well liked at the time (in part because of some anti-Madonna backlash – she was kind of everywhere in the early 90’s and her Sex book was both widely embraced and widely mocked). I like several of the songs from the album but just think this one is boring. Wouldn’t say I disliked it, I guess, just that I don’t have any real feelings attached to it one way or the other.

91. Take a Bow

From 1994’s Bedtime Stories, Second Single

By Bedtime Stories, I was sold on Madonna. I thought “Secret” was one of the most exciting pop songs of 1994 by anyone. When Madonna released her second single and it was this, I was really disappointed. Despite a fine vocal performance by Madonna and some great backing vocals by producer Babyface (its almost a duet), the song is a dreadful bore to me. I remember it used to be played endlessly on MTV and VH1 and I would get excited when I saw it was a new Madonna song and then turn it off when I realized it was this Madonna song. The video is both excellent (production value and relationship story) and appalling (glorifying bull fighting). Listening to it now, I think a lot of my dislike of this song is irrational (I’ve found myself singing it to myself a few times which leads me to think that on some level I must like it) but I cringe whenever it starts. This is a shame because its a well crafted song with, as I mentioned, excellent vocal performances. I realize this is a much-loved and well respected song, but I’m just done with it.

I’m so glad I’m done with these first 11 songs and don’t need to listen to them anymore. I like the next 90 much, much better.